Holiday houses in Eastern Oregon

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Top-rated holiday rentals in Eastern Oregon

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Guest favourite
A charming cottage from 1909 features a blue metal roof and a welcoming red door. The front porch, adorned with hanging flower baskets, invites relaxation. Surrounding greenery and gravel pathways enhance the serene outdoor setting.
Cottage in Sumpter
4.97 out of 5 average rating, 232 reviews

The Red Door Cottage. 10% off for volunteer FD

Enjoy the quintessential Eastern Oregon experience in this beautifully restored 1909 cottage. Private, elegant and super cozy in the heart of historic Sumpter Oregon. Hiking, biking, fishing, quad riding and exceptional mushroom and huckleberry picking basically any outdoor activity you can think of! Our house features two bedrooms with queen beds, full bathroom a Hideaway sofa bed, full kitchen, TV with DVDs & more. Amazing outdoor area where you can grill some delicious food, relax and enjoy!

Top Guest favourite
A scenic view from a balcony captures rows of lush vineyards stretching across a gentle landscape. The distant Blue Mountains create a serene backdrop under a clear blue sky, enhancing the tranquil atmosphere of the property.
Farm stay in Milton-Freewater
4.91 out of 5 average rating, 164 reviews

Tum A Lum Ridge Guesthouse in Walla Walla Valley

Welcome to Tum A Lum Ridge Guest House, your private retreat just minutes from downtown Walla Walla. Hidden along a private drive, our 10-acre property boasts breathtaking views of the Blue Mountains, a serene pond, and the tranquil Walla Walla River. Experience a seamless blend of luxury and nature, with outdoor spaces perfect for relaxation. Less than 1.5 miles from world-class vineyards and tasting rooms on Pepper Bridge Road, you’re ideally located for exploring the best of the wine country.

Guest favourite
A charming cabin is nestled among tall evergreen trees, surrounded by lush greenery. A stone pathway leads to the entrance, which features a wooden porch and sturdy door. The peaceful setting evokes a sense of seclusion and connection with nature.
Cabin in Donnelly
4.86 out of 5 average rating, 409 reviews

Beautiful cabin by Tamarack Resort & Cascade Lake

Stonewood Creek is the perfect combination of rustic appeal & comfortable living. The cabin sits on a stunning 1/2 acre park-like setting with a creek running through it, a tranquil 2 min walk to breathtaking view of Cascade Lake & Salmon River Mtns. First floor is a spacious studio with full bed, couch, dining area, kitchen, full bath. Separate entrance basement has full-sized bunk bed, sofa, and love seat. It is complete with fire pit, patio, walk to fishing bridge & 5 min drive to boat docks!

Guest favourite
The modern chalet is elevated on sturdy stilts, surrounded by lush greenery. The exterior features large windows and a wooden deck, providing access to the fresh mountain air and spectacular wooded views. The structure blends naturally with its forested environment.
Cabin in Joseph
4.9 out of 5 average rating, 114 reviews

Best views at Wallowa Lake- Chalet South

The Wallowa Lake Chalets are situated between Wallowa Lake and the Eagle Cap Wilderness. These Chalets have an open floor plan and were designed to encapsulate the natural surrounding beauty. The decks of the Chalets stand 26 ft above the ground creating some of the most surreal views that can be found anywhere in Wallowa County. The Chalets can be accessed by a ½ mile of rugged gravel road off of Wallowa Lake Hwy. The Chalets are about 8 min. from Joseph, OR. Follow us @wallowa_lake_chalets

Top Guest favourite
A cozy yurt is surrounded by tall pine trees, featuring a wooden deck with steps leading up to the entrance. A picnic table is positioned nearby on a gravel area, providing an outdoor space for relaxation.
Yurt in Enterprise
4.98 out of 5 average rating, 111 reviews

Ruby Pines Vacation Yurt

Cozy yurt off the beaten path yet close to beautiful Wallowa Lake, the charming town of Joseph, and all the beauty the surrounding Wallowa Mountains have to offer. We are nestled in the pine forests about 5 miles from the towns of Joseph and Enterprise. This space is ideal for a peaceful getaway for a couple, a few friends, or a family with small children. The yurt shares a driveway with the hosts’ primary residence. Please respect the neighborhood and house rules and enjoy your stay!

Top Guest favourite
The new log cabin features a sloped metal roof and large windows that fill the exterior with natural light. A spacious covered porch is lined with colorful chairs, offering a place to enjoy the outdoor views of the surrounding trees and hills.
Cabin in Harney County
4.98 out of 5 average rating, 112 reviews

Steens View Cabin at Frenchglen

★­ Located on the edge of the Malheur National Wildlife Refuge and Steens Mountain ★ Nestled in the trees with lots of privacy ★ Within easy walking distance of "downtown" Frenchglen ★­ Access to birding, photography, fishing, hiking, mtn biking, ATV riding, hunting, etc. ★ Brand new log cabin ★ Fully equipped kitchen ★ Family friendly ★­ Central air conditioning ★­ 50 amp outlet for charging electric vehicles ★ Smoking is NOT permitted anywhere on the property, and it's strictly enforced.

Top Guest favourite
A rustic cabin constructed from hand-milled wood is illuminated by a warm light at dusk. The front porch features log benches and a welcoming entrance, set against a backdrop of a serene twilight sky, with soft clouds hinting at the approaching night.
Farm in Diamond
4.98 out of 5 average rating, 100 reviews

Cowboy Cabin-1 Bedroom with Porch & BBQ

Enjoy star gazing, high desert views in this small hand hewn cabin, a unique overnight stay. We are located in REMOTE Southeastern Oregon, the cabin is on the premises of Steens Mountain Guest Ranch. A Wi-Fi repeater is available in the cabin (if the weather is stormy the Wi-Fi can be spotty). Phone service and shopping areas getting here are few & far between. This is rural living. Enjoy the quietness of the country and a beautiful sage brush view. Friendly reminder: no pets in cabin.

Top Guest favourite
A rustic A-frame cabin is nestled among tall evergreens, featuring a deep red exterior with large windows allowing natural light inside. The surrounding area showcases a natural forest floor with scattered leaves and a prominent rock near the cabin's entrance.
Cabin in Baker City
4.93 out of 5 average rating, 442 reviews

Enchanting A-Frame

Unplug! A Private Rustic Cabin 15 min. from Baker City, nestled in the foothills of the Elkhorn Mountains. Ready for a bit of adventure? Outgoing plumbing only (no running water). Bucket your washing/flushing water from the creek off of the back deck which runs most of the year. 45 min. to Anthony Lakes Ski Resort. Guests are to clean up after themselves upon checkout. No internet, TV service or Freezer. Cell service may be sketchy. 4 wheel drive for winter access Dec - March.

Top Guest favourite
A unique treehouse structure is surrounded by lush greenery, with a wooden walkway leading to the entrance. The exterior features a blend of dark wood and green siding, highlighting its harmonious integration with the forested environment.
Treehouse in Banks
4.97 out of 5 average rating, 106 reviews

Modern & Cozy TinyHome Treehouse

Escape to a hand-crafted sanctuary nestled among towering Ponderosa pines. This exclusive tiny-home-treehouse, meticulously designed over two and a half years, features a majestic tree, aptly named Mondo Pondo, that gracefully intersects the living space, blurring the line between indoors and out. Bathed in natural light, the space creates a cozy and clean ambiance, inviting you to unwind and reconnect with nature. Perfect for romantic retreats or a serene escape from the ordinary.

Top Guest favourite
A gravel road is visible leading to a rustic entrance gate marked with a sign for 'High Desert Hideaway.' The landscape features open fields and distant structures under a clear blue sky, with dry grasses lining the path and surrounding area.
Farm stay in Burns
4.94 out of 5 average rating, 295 reviews

High Desert Hideaway

Pets allowed inside if potty trained. Just a 5.3 miles from town. It is on the south side of Highway 20 east of Burns, you must go past Red Barn Road. There is red reflectors to help find the driveway at night. It’s a on a pivot that with permission and caution about buildings, pivot, equipment and the highway you may shoot ground squirrels and jack rabbits! There is a corral for horses and a kennel for dogs. It is centrally located for horse activities like cuttings, brandings.

Top Guest favourite
A private deck features wooden flooring and a railing, providing unobstructed views of rolling hilltops and a vast sky. Two wooden chairs are positioned for relaxation, creating a serene spot to enjoy the surrounding landscape.
Guesthouse in White Bird
5 out of 5 average rating, 207 reviews

Million dollar view of Salmon River Valley

The guest house is nestled on a hillside overlooking the Salmon River, Hammer Creek Park and public boat launch. It’s a one hour drive to Hells Canyon boat launch at Pittsburg Landing on the Snake River. Both areas are great for boating, rafting, and fishing. This studio guest house comfortably sleeps 4 with a queen sized bed, comfortable pull out couch, and separate full bathroom & shower. The unit also has a kitchen and private deck to enjoy the wildlife and million dollar view!

Guest favourite
The cabin is nestled among snow-covered trees, showcasing a welcoming entrance with a sloped roof and large porch. A decorative emblem is visible on the front wall. Fresh snowfall blankets the ground, enhancing the natural surroundings.
Cabin in Sumpter
4.9 out of 5 average rating, 379 reviews

Lazy Moose Cabin

Looking for a vacation rental cabin in Sumpter, Oregon? Well, look no more! The Lazy Moose Cabin is a vacation rental cabin that offers lodging accommodations year-round. The Lazy Moose Cabin offers an intimate retreat for 2. The cabin is tastefully decorated in a wildlife theme and is outfitted and supplied with just about anything you will need for your fun vacation in Sumpter. The cabin is located in the City Limits just 3 blocks east of the Downtown District.

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